Chester Holidays from £737
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Chester Holiday
The best way to experience this vibrant city is with a custom-made Chester holiday package. Stay in the neighbourhood of Essex Village, which is good for walking, hiking and views or choose someplace else — our packages are all about you. Essex Steam Train, Goodspeed Opera House and Essex Island Marina are just some of the many sights you'll want to check out during your trip to Chester. Check out Expedia's extensive range of travel options and begin planning your perfect holiday to Chester now.
Top Chester Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Landing Apartments New Haven Near Dixwell
Newhallville
£957
per person
26 Oct - 30 Oct
just found
Return flight included
London (LON) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on 25 May 2026
New Haven Hotel
Downtown New Haven
£774
per person
26 Oct - 30 Oct
just found
Return flight included
London (LON) to New Haven (HVN)
9.2/10 Wonderful! (2,259 reviews)
Modern, nice looking hotel. Very clean for the most part. Didn’t like that our bathtub had a slip proof mat that had rust color streaks all across it. Only real complaint, oh and the their coffee maker wasn’t working. Our room was also located near the ice machine and we could hear the ice being dropped regularly. That was pretty annoying once we got in bed. I would stay here again though, just don’t want a room near ice machine.
Reviewed on 13 Aug 2026
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Population | 1,550 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Harveys Beach, Goodspeed Opera House and Devils Hopyard State Park |
Top hotels in Chester
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
£55
3 Sept - 4 Sept
includes taxes & fees
7.2/10 Good! (1,030 reviews)
"Excellent service great staff"
Reviewed on 13 Aug 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
£87
23 Aug - 24 Aug
includes taxes & fees
8/10 Very good! (1,002 reviews)
"Great location & convenient to everything. Shawn (I believe his name was) was so helpful & friendly! Older place but was good for 1 night."
Reviewed on 12 Aug 2026
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
£86
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (2,759 reviews)
"Need to be aware of problems that come with the aging of the place… some renovations needed"
Reviewed on 13 Aug 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Chester attractions
Norma Terris Theater
The Norma Terris Theatre is Goodspeed Musicals' developmental space where innovative productions debut. In this intimate setting, audiences witness tomorrow's Broadway hits evolve before their eyes.
Frequently asked questions
How much does a Chester travel package cost?
Maybe less than you imagined — from a low £737, actually! By bundling flights, hotels and car rentals into a custom-built package, your trip to Chester is only clicks away.
If I'm not able to travel, can I cancel my Chester travel package?
You can. We totally understand that even the best-laid plans can fail, so we're here to help if you have to make changes to your Chester travel package. It may be possible to cancel or amend your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Chester?
Combine your bookings with Expedia to save big on your next trip. With over 550 air carriers and 1,000,000 properties across the globe, your Chester travel package can be tailored exactly to suit your budget. With all that extra money, why not include one or more interesting tours and activities? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Chester is much closer than you thought!
Does Expedia offer Book Now, Pay Later Chester holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book an incredible getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Check out these flexible payment options:
- Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
- Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: Pressing the "book now" button is easier with this option. Just put down a small deposit on your booking and then start working on your travel itinerary.
Where should I stay in Chester?
With loads to explore in Chester, we suggest you stay near its attractions. Norma Terris Theatre, Chester Creek Marina and Plattwood Park are some good ones to add to your itinerary.
What are the top hotels in Chester?
Saybrook Point Resort & Marina and Pier Blue Inn Old Saybrook - Essex are among the most popular hotels in Chester. Why not check out the amenities and facilities at each and then make a decision?
How far in advance should I book my Chester holiday?
Search Expedia to compare international flights as soon as you know your travel dates. You can generally purchase a ticket up to a year prior to departure. If you can't find your preferred air carrier, or you're booking late, fear not. Cheap tickets to Chester sometimes appear a few weeks before the date of departure.
What does an Expedia Chester travel package include?
From hotels and flights to rental cars, Expedia can help you put together a Chester package that's ideal for you. Heading away for a few weeks? Check out a rental car, flight and hotel bundle. If you're taking a short break, a flight and hotel deal may suit you better. Experiences can also be added once you've made your booking. Our packages make it a breeze to save and plan.
What should I know before booking a Chester travel package?
Tailor deals that fit your budget with an Expedia package. Hotels, flights, rental cars — we've got everything you need to plan your getaway. You'll save a packet just for bundling your bookings. Whether you're going on a snow and ski adventure or drinking cocktails on a beach, your ideal getaway is only clicks away.
Can I choose my airline with a Chester Expedia travel package?
Yes, so take your pick! We have access to over 550 airlines around the world, so you can design your Chester getaway according to your style and budget.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
